3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles

ABSTRACT

3-(4,5-Dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formula I                    
     in which R 4  is C 1 -C 4 -haloalkyl and R 1  to R 3  and R 5  to R 10  are as defined in the description are described. The compounds have herbicidal activity.

The present invention relates to certain3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles and toprocesses for their preparation, to compositions comprising them and tothe use of these derivatives or of the compositions comprising them forcontrolling harmful plants.

The literature, for example WO 96/26206, WO 98/31682 and WO 98/31681,discloses pyrazol-4-yl-benzoyl derivatives.

The earlier applications WO 00/34273, WO 00/34272, DE 19936520.2 and DE19936518.0 describe, inter alia, (4,5-dihydroisoxazol-3-yl)-substitutedbenzoylpyrazoles and their herbicidal properties. They do not describethe compounds of the formula I defined below.

However, the herbicidal properties of the prior-art compounds and theircompatibility with crop plants are not entirely satisfactory. It is anobject of the present invention to provide novel, in particularherbicidally active, compounds having improved properties.

We have found that this object is achieved by the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formulaI

in which

R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;

R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl,halogen, cyano or nitro;

R³ is hydrogen, C₁-C₆-alkyl or halogen;

R⁴ is C₁-C₄-haloalkyl;

R⁵, R⁶, R⁷ independently of one another are hydrogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl;

R⁸ is hydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylcarbonyloxy, phenyl-C₁-C₄-alkoxy,phenylcarbonyl-C₁-C₄-alkoxy, phenylsulfonyloxy or phenylcarbonyloxy,where the phenyl radical of the four lastmentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

R⁹ is hydrogen or C₁-C₂-alkyl; and

R¹⁰ is hydrogen or C₁-C₄-alkyl;

and their agriculturally useful salts.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal action. Moreover, we havefound processes for preparing these compositions and methods forcontrolling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they are presentas enantiomer or diastereomer mixtures. The invention provides both thepure enantiomers or diastereomers and their mixtures.

Compounds of the formula I may also be present in the form of theiragriculturally useful salts, the nature of the salt generally beingimmaterial. In general, the salts of those cations or the acid additionsalts of those acids are suitable whose cations and anions,respectively, do not adversely affect the herbicidal action of thecompounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, where,if desired, one to four hydrogens may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfoniumand sulfoxonium ions, preferably tri (C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R¹-R¹⁰ or asradicals on phenyl rings are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy,alkylcarbonyloxy, alkylsulfonyloxy, alkylthio, alkylsulfinyl,haloalkylsulfinyl, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl,alkenyl, alkenyloxy, phenylalkyl, phenylcarbonylalkyl, phenylalkoxy andphenylcarbonylalkoxy moieties can be straight-chain or branched. Unlessindicated otherwise, halogenated substituents preferably carry one tofive identical or different halogen atoms. The term halogen denotes ineach case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₂-alkyl, and the alkyl moieties of phenyl-C₁-C₂-alkyl andphenylcarbonyl-C₁-C₂-alkyl: methyl or ethyl;

C₁-C₄-alkyl, and the alkyl moieties of C₁-C₄-alkylcarbonyl,C₁-C₄-alkylcarbonyloxy, phenyl-C₁-C₄-alkyl andphenylcarbonyl-C₁-C₄-alkyl: C₁-C₂-alkyl as mentioned above, and alsopropyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and1,1-dimethylethyl;

C₁-C₆-alkyl, and the alkyl moieties of C₁-C₆-alkylcarbonyl andC₁-C₆-alkylcarbonyloxy: C₁-C₄-alkyl as mentioned above, and also, forexample, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-3-methylpropyl;

C₁-C₂-haloalkyl: a C₁-C₂-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,bromomethyl, iodomethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl;

C₁-C₄-haloalkyl: C₁-C₂-haloalkyl as mentioned above, and also, forexample, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl,2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl;

C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above, and also, forexample, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,6-iodohexyl or dodecafluorohexyl;

C₁-C₂-alkoxy as alkoxy moieties of phenyl-C₁-C₂-alkoxy andphenylcarbonyl-C₁-C₂-alkoxy: methoxy or ethoxy;

C₁-C₄-alkoxy, and the alkoxy radicals of phenyl-C₁-C₄-alkoxy andphenylcarbonyl-C₁-C₄-alkoxy: C₁-C₂-alkoxy as mentioned above, and also,for example, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,2-methylpropoxy and 1,1-dimethylethoxy;

C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above, and also, for example,pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy,1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy,2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy and nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above, and also, forexample, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy,6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;

C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio,1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and1,1-dimethylethylthio;

C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above, and also, forexample, pentylthio, 1-methylbutylthio, 2-methylbutylthio,3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or1-ethyl-2-methylpropylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio,2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio andnonafluorobutylthio;

C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthio as mentioned above, 25 andalso, for example, 5-fluoropentylthio, 5-chloropentylthio,5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio,6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthioor dodecafluorohexylthio;

C₁-C₆-alkylsulfinyl (C₁-C₆-alkyl-S(═O)—): for example methylsulfinyl,ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl,1-methylpropylsulfinyl, 2-methylpropylsulfinyl,1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;

C₁-C₆-haloalkylsulfinyl: a C₁-C₆-alkylsulfinyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethylsulfinyl,difluoromethylsulfinyl, trifluoromethylsulfinyl,chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl,2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl,2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl,heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl,1-(chloromethyl)-2-chloroethylsulfinyl,1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, nonafluorobutylsulfinyl,5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl,5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl,6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl ordodecafluorohexylsulfinyl;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂—), and the alkylsulfonylmoieties of C₁-C₄-alkylsulfonyloxy: for example methylsulfonyl,ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl and1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl, and the alkylsulfonyl moieties ofC₁-C₆-alkylsulfonyloxy: a C₁-C₄-alkylsulfonyl radical as mentionedabove, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁-C₆-haloalkylsulfonyl: a C₁-C₆-alkylsulfonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, i.e., for example, fluoromethylsulfonyl,difluoromethylsulfonyl, trifluoromethylsulfonyl,chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl,3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(chloromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl,5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl,5-iodopentylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl ordodecafluorohexylsulfonyl;

C₃-C₆-alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy,1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy,1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy,1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy,penten-2-yloxy, penten-3-yloxy, penten-4-yloxy,1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy,hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy,1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy,3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy,1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy,3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy,1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy,3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy,1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy,3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy,1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy,1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy,1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy,1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy,2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy,1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy,2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy,1-ethyl-2-methylprop-1-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy;

C₃-C₆-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl,1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl,1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl,1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl,hex-4-en-1-yl, Hex-5-en-1-yl, 1-methylpent-1-en-1-yl,2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl,4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl,2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;

The phenyl rings of the radicals phenylalkyl, phenylcarbonylalkyl,phenylalkoxy, phenylcarbonylalkoxy, phenylsulfonyl, phenylsulfonyloxy,phenylcarbonyl and phenylcarbonyloxy are preferably unsubstituted orcarry one to three halogen atoms and/or one nitro group, one cyanogroup, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxygroups.

In the formula I,

R¹ is preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy; inparticular C₁-C₆-alkyl; particularly preferably C₁-C₄-alkyl, mostpreferably methyl;

R² is preferably C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, halogen or nitro;in particular C₁-C₆-haloalkyl, preferably difluoromethyl ortrifluoromethyl, C₁-C₆-alkylsulfonyl, or halogen, preferably fluorine orchlorine; particularly preferably C₁-C₄-alkylsulfonyl, most preferablymethylsulfonyl and ethylsulfonyl;

R³ is preferably hydrogen, C₁-C₄-alkyl or halogen; in particularhydrogen, methyl or chlorine; particularly preferably hydrogen;

R⁴ is preferably C₁-C₂-haloalkyl; in particular fluoromethyl,chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl,1-chloro-1-ethyl, 1-fluoro-1-ethyl or pentafluoroethyl;

R⁵ is preferably hydrogen, C₁-C₂-alkyl or C₁-C₂-haloalkyl; in particularhydrogen, methyl, chloromethyl or trifluoromethyl; particularlypreferably hydrogen, methyl or chloromethyl;

R⁶ is preferably hydrogen or C₁-C₄-alkyl; in particular hydrogen ormethyl;

R⁷ is preferably hydrogen or C₁-C₄-alkyl; in particular hydrogen ormethyl;

R⁸ is preferably hydrogen or C₁-C₄-alkyl; in particular hydrogen ormethyl; is preferably hydroxyl, C₁-C₆-alkoxy, C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylcarbonyloxy, phenyl-C₁-C₂-alkoxy,phenylcarbonyl-C₁-C₂-alkoxy, phenylsulfonyloxy, phenylcarbonyloxy, wherethe phenyl radical of the four lastmentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

in particular hydroxyl, phenyl-C₁-C₂-alkoxy,phenylcarbonyl-C₁-C₂-alkoxy, phenylsulfonyloxy, phenylcarbonyloxy, wherethe phenyl radical of the four lastmentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;

particularly preferably hydroxyl;

R⁹ is preferably methyl or ethyl;

R¹⁰ is preferably hydrogen or C₁-C₄-alkyl;

in particular hydrogen, methyl or ethyl;

particularly preferably hydrogen or methyl.

Particular preference is given to the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formulaI where

R⁴ is fluoromethyl, chloromethyl, bromomethyl, difluoromethyl,trifluoromethyl, 1-chloro-1-ethyl, 1-fluoro-1-ethyl or pentafluoroethyl;

is in particular fluoromethyl, chloromethyl, bromomethyl, difluoromethylor trifluoromethyl.

Extraordinary preference is given to the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formulaI where

R¹ is C₁-C₄-alkyl;

R² is C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, halogen or nitro; and

R³ is hydrogen.

Extraordinary preference is likewise given to the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formulaI where

R⁸ is hydroxyl, phenyl-C₁-C₂-alkoxy, phenylcarbonyl-C₁-C₂-alkoxy,phenylsulfonyloxy, phenylcarbonyloxy, where the phenyl radical of thefour lastmentioned substituents may be partially or fully halogenatedand/or may carry one to three of the following groups: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

Extraordinary preference is given to the compounds of the formula Ia1(≡I where R³═H; R⁸═OH; R⁹═CH₃ and R¹⁰═H), in particular to the compoundsIa1.1 to Ia1.72 of Table 1, where the definitions of the radicals R¹ toR¹⁰ are of particular importance for the compounds according to theinvention not only in combination with one another, but in each casealso on their own.

TABLE 1 No. R¹ R² R⁴ R⁵ R⁶ R⁷ Ia1.1 CH₃ SO₂CH₃ CH₂F H H H Ia1.2 CH₃SO₂CH₃ CH₂F CH₂F H H Ia1.3 CH₃ SO₂CH₃ CH₂F CH₃ H H Ia1.4 CH₃ SO₂CH₃CH₂Cl H H H Ia1.5 CH₃ SO₂CH₃ CH₂Cl CH₂Cl H H Ia1.6 CH₃ SO₂CH₃ CH₂Cl CH₃H H Ia1.7 CH₃ SO₂CH₃ CH₂Br H H H Ia1.8 CH₃ SO₂CH₃ CH₂Br CH₃ H H Ia1.9CH₃ SO₂CH₃ CHF₂ H H H Ia1.10 CH₃ SO₂CH₃ CHF₂ CH₃ H H Ia1.11 CH₃ SO₂CH₃CHF₂ CHF₂ H H Ia1.12 CH₃ SO₂CH₃ CF₃ H H H Ia1.13 CH₃ SO₂CH₃ CF₃ CF₃ H HIa1.14 CH₃ SO₂CH₃ CF₃ CH₃ H H Ia1.15 CH₃ SO₂CH₃ CHClCH₃ H H H Ia1.16 CH₃SO₂CH₃ CHBrCH₃ H H H Ia1.17 CH₃ SO₂CH₃ CHFCH₃ H H H Ia1.18 CH₃ SO₂CH₃CF₂CF₃ H H H Ia1.19 CH₃ CF₃ CH₂F H H H Ia1.20 CH₃ CF₃ CH₂F CH₂F H HIa1.21 CH₃ CF₃ CH₂F CH₃ H H Ia1.22 CH₃ CF₃ CH₂Cl H H H Ia1.23 CH₃ CF₃CH₂Cl CH₂Cl H H Ia1.24 CH₃ CF₃ CH₂Cl CH₃ H H Ia1.25 CH₃ CF₃ CH₂Br H H HIa1.26 CH₃ CF₃ CH₂Br CH₃ H H Ia1.27 CH₃ CF₃ CHF₂ H H H Ia1.28 CH₃ CF₃CHF₂ CH₃ H H Ia1.29 CH₃ CF₃ CHF₂ CHF₂ H H Ia1.30 CH₃ CF₃ CF₃ H H HIa1.31 CH₃ CF₃ CF₃ CF₃ H H Ia1.32 CH₃ CF₃ CF₃ CH₃ H H Ia1.33 CH₃ CF₃CHClCH₃ H H H Ia1.34 CH₃ CF₃ CHBrCH₃ H H H Ia1.35 CH₃ CF₃ CHFCH₃ H H HIa1.36 CH₃ CF₃ CF₂CF₃ H H H Ia1.37 CH₂CH₃ SO₂CH₃ CH₂F H H H Ia1.38CH₂CH₃ SO₂CH₃ CH₂F CH₂F H H Ia1.39 CH₂CH₃ SO₂CH₃ CH₂F CH₃ H H Ia1.40CH₂CH₃ SO₂CH₃ CH₂Cl H H H Ia1.41 CH₂CH₃ SO₂CH₃ CH₂Cl CH₂Cl H H Ia1.42CH₂CH₃ SO₂CH₃ CH₂Cl CH₃ H H Ia1.43 CH₂CH₃ SO₂CH₃ CH₂Br H H H Ia1.44CH₂CH₃ SO₂CH₃ CH₂Br CH₃ H H Ia1.45 CH₂CH₃ SO₂CH₃ CHF₂ H H H Ia1.46CH₂CH₃ SO₂CH₃ CHF₂ CH₃ H H Ia1.47 CH₂CH₃ SO₂CH₃ CHF₂ CHF₂ H H Ia1.48CH₂CH₃ SO₂CH₃ CF₃ H H H Ia1.49 CH₂CH₃ SO₂CH₃ CF₃ CF₃ H H Ia1.50 CH₂CH₃SO₂CH₃ CF₃ CH₃ H H Ia1.51 CH₂CH₃ SO₂CH₃ CHClCH₃ H H H Ia1.52 CH₂CH₃SO₂CH₃ CHBrCH₃ H H H Ia1.53 CH₂CH₃ SO₂CH₃ CHFCH₃ H H H Ia1.54 CH₂CH₃SO₂CH₃ CF₂CF₃ H H H Ia1.55 CH₃ SO₂CH₂CH₃ CH₂F H H H Ia1.56 CH₃ SO₂CH₂CH₃CH₂F CH₂F H H Ia1.57 CH₃ SO₂CH₂CH₃ CH₂F CH₃ H H Ia1.58 CH₃ SO₂CH₂CH₃CH₂Cl H H H Ia1.59 CH₃ SO₂CH₂CH₃ CH₂Cl CH₂Cl H H Ia1.60 CH₃ SO₂CH₂CH₃CH₂Cl CH₃ H H Ia1.61 CH₃ SO₂CH₂CH₃ CH₂Br H H H Ia1.62 CH₃ SO₂CH₂CH₃CH₂Br CH₃ H H Ia1.63 CH₃ SO₂CH₂CH₃ CHF₂ H H H Ia1.64 CH₃ SO₂CH₂CH₃ CHF₂CH₃ H H Ia1.65 CH₃ SO₂CH₂CH₃ CHF₂ CHF₂ H H Ia1.66 CH₃ SO₂CH₂CH₃ CF₃ H HH Ia1.67 CH₃ SO₂CH₂CH₃ CF₃ CF₃ H H Ia1.68 CH₃ SO₂CH₂CH₃ CF₃ CH₃ H HIa1.69 CH₃ SO₂CH₂CH₃ CHClCH₃ H H H Ia1.70 CH₃ SO₂CH₂CH₃ CHBrCH₃ H H HIa1.71 CH₃ SO₂CH₂CH₃ CHFCH₃ H H H Ia1.72 CH₃ SO₂CH₂CH₃ CF₂CF₃ H H H

Extraordinary preference is also given to the compounds of the formulaIa2, in particular the compounds Ia2.1 to Ia2.72 which differ from thecorresponding compounds Ia1.1 to Ia1.72 in that R⁹ is ethyl.

Extraordinary preference is also given to the compounds of the formulaIa3, in particular the compounds Ia3.1 to Ia3.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R¹⁰ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa4, in particular the compounds Ia4.1 to Ia4.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R⁹ is ethyl and R¹⁰ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa5, in particular the compounds Ia5.1 to Ia5.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R⁸ is phenylcarbonyloxy.

Extraordinary preference is also given to the compounds of the formulaIa6, in particular the compounds Ia6.1 to Ia6.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R⁸ is phenylcarbonyloxy and R⁹ isethyl.

Extraordinary preference is also given to the compounds of the formulaIa7, in particular the compounds Ia7.1 to Ia7.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R⁸ is phenylcarbonyloxy and R¹⁰ ismethyl.

Extraordinary preference is also given to the compounds of the formulaIa8, in particular the compounds Ia8.1 to Ia8.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R⁸ is phenylcarbonyloxy, R⁹ is ethyland R¹⁰ is methyl.

Extraordinary preference is also given to the compounds of the formulaIa9, in particular the compounds Ia9.1 to Ia9.72 which differ from thecompounds Ia1.1 to Ia1.72 in that R⁸ is 3-fluorophenylcarbonyloxy.

Extraordinary preference is also given to the compounds of the formulaIa10, in particular the compounds Ia10.1 to Ia10.72 which differ fromthe compounds Ia1.1 to Ia1.72 in that RB is 3-fluorophenylcarbonyloxyand R⁹ is ethyl.

Extraordinary preference is also given to the compounds of the forrmulaIa11, in particular the compounds Ia11.1 to Ia11.72 which differ fromthe compounds Ia1.1 to Ia1.72 in that R⁸ is3-trifluoromethylphenylcarbonyloxy.

Extraordinary preference is also given to the compounds of the formulaIa12, in particular the compounds Ia12.1 to Ia12.72 which differ fromthe compounds Ia1.1 to Ia1.72 in that R⁸ is 3-trifluorophenylcarbonyloxyand R⁹ is ethyl.

Extraordinary preference is also given to the compounds of the formulaIa13, in particular the compounds Ia13.1 to Ia13.72 which differ fromthe compounds Ia1.1 to Ia1.72 in that R⁸ is 3-chlorophenylcarbonyloxy.

Extraordinary preference is also given to the compounds of the formulaIa14, in particular the compounds Ia14.1 to Ia14.72 which differ fromthe compounds Ia1.1 to Ia1.72 in that R⁸ is 3-chlorophenylcarbonyloxyand R⁹ is ethyl.

The 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of theformula I can be obtained by various routes, for example by theprocesses below.

Reaction of pyrazoles of the formula II with an activated benzoic acidderivative IIIα or a benzoic acid IIIβ, which is preferably activated insitu, to give the corresponding acylation product I′ and subsequentrearrangement affords compounds of the formula I where R⁸═OH.

L¹ is a nucleophilically displaceable leaving group, such as halogen,for example bromine or chlorine, hetaryl, for example imidazolyl orpyridyl, carboxylate, for example acetate, trifluoroacetate, etc.

The activated benzoic acid can be employed directly, such as in the caseof the benzoyl halides, or be generated in situ, for example usingdicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester,2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in thepresence of a base. The reactants and the auxiliary base areadvantageously employed in this case in equimolar amounts. A slightexcess of auxiliary base, for example from 1.2 to 1.5 molar equivalents,based on II, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Suitable for use as solvents are, for example,chlorinated hydrocarbons, such as methylene chloride,1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene,chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether,dimethoxyethane, tetrahydrofuran, dioxane, polar aprotic solvents, suchas acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, suchas ethyl acetate, or mixtures of these.

If the activated carboxylic acid component used is a benzoyl halide, itmay be advantageous to cool the reaction mixture to 0-10° C. when addingthis reaction partner. The mixture is subsequently stirred at 20-100°C., preferably at 25-50° C., until the reaction has ended. Work-up iscarried out in a customary manner, for example by pouring the reactionmixture into water and extracting the product of value. Solvents whichare particularly suitable for this purpose are methylene chloride,diethyl ether, dimethoxyethane and ethyl acetate. The organic phase isdried and the solvent is removed, after which the crude ester I′ can beemployed for the rearrangement without any further purification.

The rearrangement of the esters I′ to the compounds of the formula I isadvantageously carried out at 20-40° C. in a solvent and in the presenceof a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride,1,2-dichloroethane, dioxane, ethyl acetate, dimethoxyethane,tetrahydrofuran, toluene or mixtures of these. Preferred solvents areacetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine or pyridine oralkali metal carbonates, such as sodium carbonate or potassiumcarbonate, which are preferably employed in an equimolar amount or an upto four-fold excess, based on the ester. Preference is given to usingtriethylamine or alkali metal carbonates, preferably in twice theequimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanideand potassium cyanide, and organic cyano compounds, such as acetonecyanohydrin and trimethylsilyl cyanide. They are employed in an amountof from 1 to 50 mol percent, based on the ester. Preference is given tousing acetone cyanohydrin or trimethylsilyl cyanide, for example in anamount of from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up can be carried out in a manner known per se. The reactionmixture is, for example, acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, for example methylene chloride or ethyl acetate. Theorganic extract can be extracted with 5-10% strength alkali metalcarbonate solution, for example sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified and the resulting precipitateis filtered off with suction and/or extracted with methylene chloride orethyl acetate, dried and concentrated. (Examples for the preparation ofesters of hydroxypyrazoles and for the rearrangement of the esters aregiven, for example, in EP-A 282 944 and U.S. Pat No. 4,643,757).

However, it is also possible to generate the “acylation product” I′ insitu by reacting a pyrazole of the formula II, or an alkali metal saltthereof with a 3-(4,5-dihydroisoxazol-3-yl)benzene derivative of theformula IV in the presence of carbon monoxide, a catalyst and a base.

L² is a leaving group, such as halogen, for example chlorine, bromine oriodine, or sulfonate, such as mesylate or triflate; preference is givento bromine or triflate.

The “acylation product” I′ proceeds to react under the reactionconditions, generally directly, to give the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole of the formulaI.

Suitable catalysts are palladium-ligand complexes in which the palladiumis present in oxidation state 0, metallic palladium, which hasoptionally been absorbed on a carrier, and preferably palladium(II)salts. The reaction with palladium(II) salts and metallic palladium ispreferably carried out in the presence of complex ligands.

An example of a suitable palladium(0)-ligand complex istetrakis(triphenylphosphine)palladium.

Metallic palladium is preferably absorbed on an inert carrier such as,for example, activated carbon, silica, alumina, barium sulfate orcalcium carbonate. The reaction is preferably carried out in thepresence of complex ligands such as, for example, triphenylphosphine.

Examples of suitable palladium(II) salts are palladium acetate andpalladium chloride. The presence of complex ligands such as, forexample, triphenylphosphine is preferred.

Suitable complex ligands for the palladium-ligand complexes, or in whosepresence the reaction is preferably carried out with metallic palladiumor palladium(II) salts, are tertiary phosphines whose structure isrepresented by the following formulae:

where z is 1 to 4 and the radicals R^(a) to R^(g) are C₁-C₆-alkyl,C₃-C₆-cycloalkyl, aryl-C₁-C₂-alkyl or, preferably, aryl. Aryl is, forexample, naphthyl and unsubstituted or substituted phenyl such as, forexample, 2-tolyl and, in particular, unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per sestarting from commercially available palladium salts such as palladiumchloride or palladium acetate and the appropriate phosphines such as,for example, triphenylphosphine, tricyclohexylphosphine, or1,2-bis(diphenylphosphino)ethane. Many of the complexed palladium saltsare also commercially available. Preferred palladium salts are[(R)(+)2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II)chloride, bis(triphenylphosphine)palladium(II) acetate and, inparticular, bis(triphenylphosphine)palladium(II) chloride.

The palladium catalyst is usually employed in a concentration of from0.05 to 5 mol%, and preferably 1-3 mol%.

Suitable bases are tertiary amines, such as, for example,N-methylpiperidine, ethyldiisopropylamine,1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Alsosuitable is alkali metal carbonate, such as sodium carbonate orpotassium carbonate. However, mixtures of potassium carbonate andtriethylamine are also suitable.

In general, from 2 to 4 molar equivalents, in particular 2 molarequivalents, of the alkali metal carbonate, and from 1 to 4 molarequivalents, in particular 2 molar equivalents, of the tertiary amineare employed, based on the 3-(4,5-dihydroisoxazo-3-yl)benzene derivativeof the formula IV.

Suitable solvents are nitriles, such as benzonitrile and acetonitrile,aromatic hydrocarbons, such as toluene, amides, such asdimethylformamide, dimethylacetamide, tetra-C₁-C₄-alkylureas orN-methylpyrrolidone and, preferably, ethers, such as tetrahydrofuran andmethyl tert-butyl ethers. Particular preference is given to ethers, suchas 1,4-dioxane and dimethoxyethane.

Compounds of the formula I where R⁸hydroxyl are obtained by reactingcompounds of the formula I where R⁸=hydroxyl with alkylating agents,sulfonylating agents or acylating agents L³-R^(8a) (V)

L³ is a nucleophilically displaceable leaving group, such as halogen,for example bromine or chlorine, acyloxy, for example acetyloxy orethylcarbonyloxy, or alkylsulfonyloxy, for example methylsulfonyloxy ortrifluoromethylsulfonyloxy.

R^(8a) is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylcarbonyl, phenyl-C₁-C₄-alkyl, phenylcarbonyl-C₁-C₄-alkyl,phenylsulfonyl or phenylcarbonyl, where the phenyl radical of the fourlastmentioned substituents may be partially or fully halogenated and/ormay carry one to three of the following groups: nitro, cyano,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

The compounds of the formula V can be employed directly, such as, forexample, in the case of the sulfonyl halides or sulfonic anhydrides, orbe generated in situ, for example activated sulfonic acids (usingsulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole,etc.).

The starting materials are generally employed in equimolar amounts.However, it may also be advantageous to employ an excess of one or theother component.

If appropriate, it may be advantageous to carry out the reaction in thepresence of a base. The reactants and the auxiliary base areadvantageously employed in equimolar amounts. An excess of auxiliarybase, for example from 1.5 to 3 molar equivalents, based on I (whereR⁸=OH), may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, such astriethylamine, pyridine, alkali metal carbonates, for example sodiumcarbonate or potassium carbonate, and alkali metal hydrides, for examplesodium hydride. Preference is given to using triethylamine and pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, forexample toluene, xylene, chlorobenzene, ethers, such as diethyl ether,methyl tert-butyl ether, tetrahydrofuran and dioxane, polar aproticsolvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide,or esters, such as ethyl acetate, or mixtures of these.

In general, the reaction temperature is in the range from 0° C. to theboiling point of the reaction mixture.

Work-up can be carried out in a manner known per se to give the product.

The pyrazoles of the formula II used as starting materials are known orcan be prepared by processes known per se (for example EP-A 240 001 andJ. Prakt. Chem. 315, 383 (1973)).

The compounds of the formulae III and IV

where in each case the variables R¹ to R⁷ are as defined for thecompounds of the formula I and

L is hydroxyl or a radical which can be removed by hydrolysis; or

L² is a nucleophilically displaceable leaving group,

are both as such novel.

Examples of radicals which can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals, which may be substituted,halides and hetaryl radicals attached via nitrogen, amino and iminoradicals, which may be substituted, etc.

Examples of nucleophilically displaceable leaving groups are halogen,C₁-C₄-alkylsulfonyl and C₁-C₄-haloalkylsulfonyloxy.

Preferred compounds of the formula III are those in which L is halogen,in particular chlorine or bromine.

Also preferred are those compounds of the formula III in which L isC₁-C₆-alkoxy.

Preference is likewise given to those compounds of the formula III inwhich L is hydroxyl.

With respect to the variables R¹ to R⁷, the particularly preferredembodiments of the compounds of the formula III or IV correspond tothose of the 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazolesof the formula I.

The compounds of the formula III or IV can be prepared similarly toknown processes (cf. WO 96/26206, WO 98/31681 and PCT/EP99/03006). Thus,the compounds of the formula IIIβ (≡III where L=hydroxyl) or the3-(4,5-dihydroisoxazol-3-yl)benzene derivatives IV can be converted into4,5-dihydroisoxazol-3-yl derivatives III or IV by conversion of oximesof the formula VI or VII in a manner known per se via the hydroxamicacid halide intermediate, in particular via the hydroxamic acidchlorides. The latter are employed to generate nitrile oxides in situwhich are reacted with alkenes to give the desired products (cf, forexample, Chem. Ber. 106, 3258-3274 (1972)).

The compounds of the formula III (where L=C₁-C₆-alkoxy) are thenconverted in a manner known per se by hydrolysis into the benzoic acidIIIβ.

PREPARATION EXAMPLES Synthesis of the End Products Example 14-[2-Methyl-3-(5-chloromethyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoyl]-5-hydroxy-1-methyl-1H-pyrazole(Compound 2.1)

Step a)

With ice-cooling, 0.70 g (1.99 mmol) of2-methyl-3-(5-chloromethyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoylchloride in 40 ml of tetrahydrofuran was added dropwise to a mixture of0.2 g (1.99 mmol) of 1-methyl-5-hydroxy-1H-pyrazole, 0.40 g (4 mmol) oftriethylamine and 40 ml of tetrahydrofuran. After 12 hours of stirringat room temperature, the solvent was removed and the residue was takenup in ethyl acetate and washed with aqueous potassium carbonate solutionand water. The solution was then dried and the solvent was distilledoff. This gave 0.82 g of an amorphous foam which was used for furtherreactions without further purification.

Step b)

A mixture of 0.82 g of the product from step a) and 0.41 g (2.99 mmol)of potassium carbonate in 5 ml of dioxane was refluxed for five hours.After cooling and removal of the solvent, the residue was taken up inwater and washed with diethyl ether. The aqueous phase was adjusted topH 1-2 using hydrochloric acid and extracted with methylene chloride.These combined organic phases were washed with water and dried, and thesolvent was distilled off. This gave 0.69 g (84% of theory) of anamorphous powder. The ¹H-NMR spectrum found corresponded to the givenstructure of the title compound.

Synthesis of the Intermediates Example 22-Methyl-3-[5-(4-chlorobutyl)-4,5-dihydroisoxazol-3-yl]-4-methyl-sulfonylbenzoicAcid

Step a):

1-Bromo-2-methyl-3-[5-(4-chlorobutyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzene(Compound 4.1)

At room temperature, 50 ml of sodium hypochlorite solution (12.5% ofactive chlorine, admixed with a spatula tip of sodium acetate) wereadded dropwise with vigorous stirring to a solution of 15 g (51.4 mmol)of 3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime and 6.7 g (56.5mmol) of 6-chlorohexene in 200 ml of methylene chloride. The reactionmixture was stirred at room temperature overnight. The reaction mixturewas then stirred into 300 ml of water. The organic phase was washedthree times with water, dried and concentrated to dryness. This gave19.3 g of a viscous yellow oil (92.4% of theory). The ¹H-NMR spectrumcorresponds to the given structure.

Step b):

2-Methyl-3-[5-(4-chlorobutyl)-4,5-dihydroisoxazol-3-yl]-4-methyl-sulfonylbenzoicAcid (Compound 3.2)

14.5 g (35.5 mmol) of the compound obtained in step a), 0.4 g ofpalladium acetate (0.05 equivalents), 2 g of tricyclohexylphosphine (0.2equivalents), 1.5 g of lithium chloride (1 equivalent), 7.2 g oftriethylamine (2 equivalents), 100 ml of toluene and 50 ml of water werefilled into a miniature autoclave. The reaction mixture was stirred at140° C. under a carbon monoxide pressure of 20 bar for 12 hours. Aftercooling, the reaction mixture was discharged using water. The phaseswere separated, and the organic phase was extracted once with 5%strength aqueous sodium hydroxide. The combined aqueous phases werewashed twice with diethyl ether, dried and evaporated to dryness. Thisgave 3.2 g of a viscous yellow oil (24.1% of theory). The ¹H-NMRspectrum found corresponds to the given structure.

Example 32-Methyl-3-[5,5-bis(chloromethyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzoylChloride (Compound 3.4)

Step a):

1-Bromo-2-methyl-3-[5,5-di(chloromethyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzene(Compound 4.2)

At room temperature, 50 ml of sodium hypochlorite solution (whichcontained 3.8 g (51.4 mmol) of NaOCl, admixed with a spatula tip ofsodium acetate) were added dropwise with stirring to a solution of 15 g(51.4 mmol) of 3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime and7.1 g (56.5 mmol) of 2-chloromethyl-3-chloropropene in 250 ml ofmethylene chloride. The reaction mixture was stirred at room temperatureovernight. The phases were separated, and the organic phase was washedthree times with water, dried and evaporated to dryness. The residue waschromatographed on silica gel using, as mobile phase, first cyclohexane,then cyclohexane/ethyl acetate 90:10 and finally cyclohexane/ethylacetate 80:20. This gave 13.5 g of a white powder (63.3% of theory).M.p.: 144-145° C. The ¹H-NMR spectrum found corresponds to the givenstructure.

Step b):

2-Methyl-3-[5,5-bis(chloromethyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzoicAcid (Compound 3.3)

12 g (28.91 mmol) of the compound obtained in step a), 0.32 g (0.05equivalents) of palladium acetate, 1.6 g (0.2 equivalents) oftricyclohexylphosphine, 1.23 g (1 equivalent) of lithium chloride, 5.84g (2 equivalents) of triethylamine, 100 ml of toluene and 50 ml of waterwere filled into an autoclave. The autoclave was flushed six times withcarbon monoxide. The reaction mixture was then stirred at 140° C. undera carbon monoxide pressure of 20 bar for 12 hours. After cooling, thereaction mixture was discharged using water. The phases were separatedand the organic phase was extracted twice using 5% strength NaOH. Thecombined aqueous phases were washed with diethyl ether, the pH of theaqueous phase was adjusted to 1-2 and the aqueous phase was extractedthree times with methylene chloride. The organic phase was washed twicewith water, dried and concentrated to dryness. This gave 9.6 g of awhite powder (87.4% of theory). The ¹H-NMR spectrum found corresponds tothe given structure.

Step c):

2-Methyl-3-[5,5-bis(chloromethyl)-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzoylChloride (Compound 3.4)

At room temperature, 5.4 g (45.26 mmol) of thionyl chloride were addeddropwise to a solution of 8.6 g (22.63 mmol) of the compound obtained instep b) in a mixture of 150 ml of toluene and 3 drops ofdimethylformamide. The reaction mixture was stirred at room temperaturefor 6 hours and then evaporated to dryness. Three times, the residue wastaken up in methylene chloride and evaporated to dryness. This gave 9.0g of a viscous brown oil (100% of theory).

Example 41-Bromo-2-methyl-3-[5-bromomethyl-4,5-dihydroisoxazol-3-yl]-4-methylsulfonylbenzene

At 55-60° C., 2.33 g (17.1 mmol) of N-chlorosuccinimide were added inportions to a solution of 5.0 g (17.1 mmol) of3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime in 200 ml ofdimethylformamide. After 30 minutes of stirring, the reaction mixturewas cooled and introduced into ice-water, and the residue was filteredoff, washed with water and dried. The resulting product was suspended inmethylene chloride, and 1.7 g (17.1 mmol) of triethylamine and then 2.48g (20.1 mmol) of alkyl bromide were added dropwise. The reaction mixturewas stirred at room temperature for 12 hours and then washed with waterand dried, and the solvent was removed. This gave 5.91 g of a palesolid. The ¹H-NMR spectrum found corresponded to the given structure ofthe title compound.

In addition to the compounds above, Tables 2 to 4 list further compoundsof the formulae I, III and IV which were prepared or are preparable in asimilar manner.

TABLE 2 I

physical data No. R¹ R² R³ R⁴ R⁵ R⁶ R⁷ R⁸ R⁹ R¹⁰ m.p. [° C.] 2.1 CH₃CH₃SO₂ H CH₂Cl H H H OH CH₃ H 76-78 2.2 CH₃ CH₃SO₂ H CH₂Cl H H H OHCH₂CH₃ H 73-77 2.3 CH₃ CH₃SO₂ H CH₂Cl H H H OH CH₃ CH₃ 74-77 2.4 CH₃CH₃SO₂ H CH₂Cl CH₂Cl H H OH CH₃ H 76-80 2.5 CH₃ CH₃SO₂ H CH₂Cl CH₂Cl H HOH CH₂CH₃ H 74-80 2.6 CH₃ CH₃SO₂ H CH₂Cl CH₂Cl H H OH CH₃ CH₃ 81-862.7¹⁾ CH₃ CH₃SO₂ H CH₂Cl H CH₃ H OH CH₃ H  85-100 2.8 CH₃ CH₃SO₂ H CH₂ClH CH₃ H OH CH₂CH₃ H 2.9 CH₃ CH₃SO₂ H CH₂Cl H CH₃ H OH CH₃ CH₃ 2.10 CH₃CH₃SO₂ H CH₂Cl CH₃ H H OH CH₃ H 105-110 2.11²⁾ CH₃ CH₃SO₂ H CH₂Cl H CH₃H OH CH₃ H 85-95 2.12 CH₃ CH₃SO₂ H CHF₂ H H H OH CH₃ H 73-76 2.13 CH₃CH₃SO₂ H CHF₂ H H H OH CH₂CH₃ H 71-75 ¹⁾trans-isomer ²⁾cis-isomer

TABLE 3 III

physical data No. R¹ R² R³ R⁴ R⁵ R⁶ R⁷ L m.p. [° C.] 3.1 CH₃ CH₃SO₂ HCH₂Cl H H H Cl oil 3.2 CH₃ CH₃SO₂ H (CH₂)₄Cl H H H OH oil 3.3 CH₃ CH₃SO₂H CH₂Cl CH₂Cl H H OH 3.4 CH₃ CH₃SO₂ H CH₂Cl CH₂Cl H H Cl oil 3.5 CH₃CH₃SO₂ H CH₂Cl H H H OH 43-48

TABLE 4 IV

physical data No. R¹ R² R³ R⁴ R⁵ R⁶ R⁷ L² m.p. [° C.] 4.1 CH₃ CH₃SO₂ H(CH₂)₄Cl H H H Br oil 4.2 CH₃ CH₃SO₂ H CH₂Cl CH₂Cl H H Br 144-145 4.3CH₃ CH₃SO₂ H CH₂Br H H H Br 4.4 CH₃ CH₃SO₂ H CH₂Cl H H H Br 138-140

The 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of theformula I and their agriculturally useful salts are suitable, both inthe form of isomer mixtures and in the form of the pure isomers, asherbicides. The herbicidal compositions comprising compounds of theformula I control vegetation on non-crop areas very efficiently,especially at high rates of application. They act against broad-leavedweeds and harmful grasses in crops such as wheat, rice, maize, soya andcotton without causing any significant damage to the crop plants. Thiseffect is mainly observed at low rates of application.

Depending on the application method used, the compounds of the formulaI, or the herbicidal compositions comprising them, can additionally beemployed in a further number of crop plants for eliminating undesirableplants. Examples of suitable crops are the following: Allium cepa,Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgarisspec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus,Brassica napus var. napobrassica, Brassica rapa var. silvestris,Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citruslimon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffealiberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeisguineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypiumarboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus,Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas,Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersiconlycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musaspec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa,Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Solanumtuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifoliumpratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis viniferaand Zea mays.

In addition, the compounds of the formula I may also be used in cropswhich tolerate the action of herbicides owing to breeding, includinggenetic engineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be used for example in the form of ready-to-sprayaqueous solutions, powders, suspensions, also highly-concentratedaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusts, materials for broadcasting or granules, bymeans of spraying, atomizing, dusting, broadcasting or watering. The useforms depend on the intended aims; in any case, they should guarantee avery fine distribution of the active compounds according to theinvention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I and auxiliaries which are customary for formulating crop protectionagents.

Essentially, suitable inert auxiliaries include: mineral oil fractionsof medium to high boiling point, such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, or strongly polar solvents, e.g. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles, either assuch or dissolved in an oil or solvent, can be homogenized in water bymeans of a wetting agent, tackifier, dispersant or emulsifier.Alternatively, it is possible to prepare concentrates consisting ofactive substance, wetting agent, tackifier, dispersant or emulsifierand, if desired, solvent or oil, which are suitable for dilution withwater.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, e.g.ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, andof fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene, or of the naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl ortributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active substances together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from about 0.001 to 98% by weight, preferably from0.01 to 95% by weight of at least one active compound. The activecompounds are employed in a purity of from 90% to 100%, preferably from95% to 100% (according to the NMR spectrum).

The formulation examples below illustrate the production of suchpreparations:

I. 20 parts by weight of the compound No. 2.3 are dissolved in a mixtureconsisting of 80 parts by weight of alkylated benzene, 10 parts byweight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleicacid N-monoethanolamide, 5 parts by weight of calciumdodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000parts by weight of water and finely distributing it therein gives anaqueous dispersion which comprises 0.02% by weight of the activecompound.

II. 20 parts by weight of the compound No. 2.3 are dissolved in amixture consisting of 40 parts by weight of cyclohexanone, 30 parts byweight of isobutanol, 20 parts by weight of the adduct of 7 mol ofethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of theadduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring thesolution into 100,000 parts by weight of water and finely distributingit therein gives an aqueous dispersion which comprises 0.02% by weightof the active compound.

III. 20 parts by weight of the active compound No. 2.3 are dissolved ina mixture consisting of 25 parts by weight of cyclohexanone, 65 parts byweight of a mineral oil fraction of boiling point 210 to 280° C. and 10parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound No. 2.3 are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt ofa lignosulfonic acid from a sulfite waste liquor and 60 parts by weightof pulverulent silica gel, and the mixture is ground in a hammer mill.Finely distributing the mixture in 20,000 parts by weight of water givesa spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of the active compound No. 2.3 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of the active compound.

VI. 20 parts by weight of the active compound No. 2.3 are mixedintimately with 2 parts by weight of the calcium salt ofdodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycolether, 2 parts by weight of the sodium salt of aphenol/urea/formaldehyde condensate and 68 parts by weight of aparaffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 2.3 is dissolved in a mixtureconsisting of 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. 2.3 is dissolved in a mixtureconsisting of 80 parts by weight of cyclohexanone and 20 parts by weightof Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil).This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can beapplied pre- or post-emergence. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that they come into contact as littleas possible, if at all, with the leaves of the sensitive crop plants,while the active compounds reach the leaves of undesirable plantsgrowing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of the compound of the formula I are from 0.001 to3.0, preferably from 0.01 to 1.0 kg/ha of active substance (a.s.),depending on the control target, the season, the target plants and thegrowth stage.

To widen the activity spectrum and to achieve synergistic effects, the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formulaI may be mixed with a large number of representatives of otherherbicidal or growth-regulating active compound groups and then appliedconcomitantly. Suitable components for mixtures are, for example,1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid andits derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acidsand their derivatives, benzoic acid and its derivatives,benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetarylaryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives,carbamates, quinolinecarboxylic acid and its derivatives,chloroacetanilides, cyclohexenone oxime ether derivatives, diazines,dichloropropionic acid and its derivatives, dihydrobenzofurans,dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers,dipyridyls, halocarboxylic acids and their derivatives, ureas,3-phenyluracils, imidazoles, imidazolinones,N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols,aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid andits derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formulaI, alone or else concomitantly in combination with other herbicides, orin the form of a mixture with other crop protection agents, for exampletogether with agents for controlling pests or phytopathogenic fungi orbacteria. Also of interest is the miscibility with mineral saltsolutions, which are employed for treating nutritional and trace elementdeficiencies. Non-phytotoxic oils and oil concentrates may also beadded.

Use Examples

The herbicidal activity of the 3-(4,5-dihydroisoxazol-3-yl)-substitutedbenzoylpyrazoles of the formula I was demonstrated by the followinggreenhouse experiments:

The cultivation containers used were plastic pots containing loamy sandwith approximately 3.0% of humus as the substrate. The seeds of the testplants were sown separately for each species.

For the pre-emergence treatment, directly after sowing, the activecompounds, which had been suspended or emulsified in water, were appliedby means of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this was adverselyaffected by the active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of from 3 to 15 cm, depending on the plant habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. The test plants were for this purpose either sown directly andgrown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment. The application rate for the post-emergence treatment was0.25 or 0.125 kg/ha of a.s. (active substance). Depending on thespecies, the plants were kept at 10-25° C. or 20-35° C. The test periodextended over from 2 to 4 weeks. During this time, the plants weretended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the followingspecies:

Scientific name Common name Amaranthus retroflexus pig weed Brachiariaplantaginea alexandergrass Chenopodium album lambsquaters Echinochloacrus galli barnyardgrass Polygonum persicaria ladysthumb Setaria faberigiant foxtail

At application rates of 0.25 or 0.125 kg/ha, compound 2.3 (Table 2)showed very good post-emergence action against the abovementionedundesirable plants.

We claim:
 1. A 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoleof the formula I

in which R¹ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy; R² is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl orC₁-C₆-haloalkylsulfonyl, halogen, cyano or nitro; R³ is hydrogen,C₁-C₆-alkyl or halogen; R⁴ is C₁-C₄-haloalkyl; R⁵, R⁶, R⁷ independentlyof one another are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R⁸ ishydroxyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylsulfonyloxy,C₁-C₆-alkylcarbonyloxy, phenyl-C₁-C₄-alkoxy,phenylcarbonyl-C₁-C₄-alkoxy, phenylsulfonyloxy or phenylcarbonyloxy,where the phenyl radical of the four lastmentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R⁹ is hydrogen or C₁-C₂-alkyl; and R¹⁰is hydrogen or C₁-C₄-alkyl; and its agriculturally useful salts.
 2. A3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole as claimed inclaim 1, wherein R⁴ is fluoromethyl, chloromethyl, bromomethyl,difluoromethyl, trifluoromethyl, 1-chloro-1-ethyl, 1-fluoro-1-ethyl orpentafluoroethyl.
 3. A 3-(4,5-dihydroisoxazol-3-yl)-substitutedbenzoylpyrazole as claimed in claim 1, wherein R¹ is C₁-C₄-alkyl; R² isC₁-C₆-haloalkyl, C₁-C₈-alkylsulfonyl, halogen or nitro; and R³ ishydrogen.
 4. A 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoleas claimed in claim 1, wherein R⁸ is hydroxyl, phenyl-C₁-C₂-alkoxy,phenylcarbonyl-C₁-C₂-alkoxy, phenylsulfonyloxy, phenylcarbonyloxy, wherethe phenyl radical of the four lastmentioned substituents may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 5. A process for preparing3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles as claimed inclaim 1, which comprises acylating a pyrazole of the formula II

with an activated benzoic acid IIIα or a benzoic acid IIIβ

where R¹ to R⁷, R⁹ and R¹⁰ are as defined in claim 1 and L¹ is anucleophilically displaceable leaving group; rearranging the acylationproduct to a compound of the formula I where R⁸=hydroxyl; and, ifappropriate, reacting the product of the rearrangement with a compoundof the formula V L³—R^(8a)  V where L³ is a nucleophilicallydisplaceable leaving group; and R^(8a) is C₁-C₆-alkyl, C₃-C₆-alkenyl,C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl, phenyl-C₁-C₄-alkyl,phenylcarbonyl-C₁-C₄-alkyl, phenylsulfonyl or phenylcarbonyl, where thephenyl radical of the four lastmentioned substituents may be partiallyor fully halogenated and/or may carry one to three of the followinggroups: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy.
 6. A process for preparing3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles as claimed inclaim 1, which comprises reacting a pyrazole of the formula II

in which R⁹ and R¹⁰ are as defined in claim 1, or an alkali metal saltthereof, with a 3-(4,5-dihydroisoxazol-3-yl)benzene derivative of theformula IV

where R¹ to R⁷ are as defined in claim 1 and L² is a leaving group, inthe presence of carbon monoxide, a catalyst and a base to give acompound of the formula I where R⁸=hydroxyl; and, if appropriate,reacting the reaction product with a compound of the formula VL³—R^(8a)  V where L³ and R^(8a) are as defined in claim
 5. 7. Acomposition, comprising a herbicidally effective amount of at least one3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole of the formulaI or an agriculturally useful salt of I as claimed in claim 1 andauxiliaries customarily used for formulating crop protection agents. 8.A process for preparing compositions as claimed in claim 7, whichcomprises mixing a herbicidally effective amount of at least one3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole of the formulaI or an agriculturally useful salt of I and auxiliaries customarily usedfor formulating crop protection agents.
 9. A method for controllingundesirable vegetation, which comprises allowing a herbicidallyeffective amount of at least one3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole of the formulaI or an agriculturally useful salt of I as claimed in claim 1 to act onplants, their habitat and/or on seeds.
 10. The use of the3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles of the formulaI and/or their agriculturally useful salts as claimed in claim 1 asherbicides.